Clinton, Mississippi native, Jacob Dillard debuted at the Grand Ole Opry in November 2025 as the pedal steel guitarist with Walker Montgomery’s band. While performing during the Opry’s 100th anniversary fulfilled a lifelong dream, it provided a time to reflect on the years of hard work in Mississippi and Nashville that paved the way. Landing the opportunity to play with Walker Montgomery, who is the son of country music star John Michael Montgomery, seems serendipitous.
“It all kind of fell into place about a year ago,” shared Dillard. “I was wrapping up my degree at Middle Tennessee State University, working towards a Master’s program in recording arts and technology. And I met the guitar player who was in Walker’s band, and he introduced me to them, and we hit it off really quickly, and I’ve been playing with them ever since.”
Dillard didn’t just grow up listening to country music; he has fond memories of listening to the Opry on the radio and watching the shows.
“Not only am I a fan of country music, but I’m also a really big history fan in general. And appreciate the history of country music,” shared Dillard. “So the Grand Ole Opry and the Ryman Auditorium both have a really special place in my heart. I used to tune in to WSM 650 AM to try to listen to the Opry when I could, depending on the airwaves, and I still listen to it to this day. So to be a part of one of the shows is just really special.”
Music has been a part of Dillard’s life since he was little. Dillard’s dad played bass when he was younger, and his mom played piano. The Dillard family was active in their local church’s Youth Praise Team. A young Dillard spent hours at rehearsals surrounded by different instruments, singing, and making music.
“My first instrument was the drums, when I was four or five, but my parents weren’t too pleased with the loud noises all hours of the day,” explained Dillard. “I learned a little piano from mom, but I went on to the guitar in the first grade, and really liked learning it. I played the guitar through high school, until my junior/senior year, when I was ready for something a little more challenging.”
Dillard was first introduced to a pedal steel guitar by his cousin, Jonathan Simmons, who has been playing since he was born, and by his pastor, Dr. Baker, who played one at church. A pedal steel guitar is a unique, amplified lap steel guitar that sits on legs and uses foot pedals and knee levers to mechanically change string pitches. The player uses a tone bar on the strings while their feet and knees manipulate the mechanisms for chords and melodies. Pedal steel guitars are popular in vareity of genres of music, but traditional country is where Dillard heard it first.
“My parents got me a little starter pedal steel guitar, and I fell in love with it and started playing,” shared Dillard. “I never dreamt I’d be playing it in a band and traveling to shows.”
Dillard moved to Nashville after graduating from Clinton High School with an interest in the music business.
“I wanted to get up here to learn more about the industry, and wanted to get involved somewhere. I really enjoy recording,” shared Dillard. “That’s what I went to school for: songwriting and recording.”
Although Dillard never expected to play in a band and tour the country, he’s enjoyed the opportunity. Dillard credits Casey Combest, a Clinton guitarist and the six years in Clinton High School’s Attache Show Choir, for giving him the skills and experience needed to prepare him for professional stages like the Grand Ole Opry.
*Photos courtesy of Jacob Dillard
